Sodium Hydroxide → 8-Chloro-1,1-dimethyl-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

HRID 1639378Notes

Reaction equation

HRID 1639378 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:24]=[CH:23][C:11]2[C:12]3[C:13]([CH3:22])([CH3:21])[CH2:14][C:15](=O)[NH:16][C:17]=3[CH2:18][CH2:19][C:10]=2[CH:9]=1.[OH-].[Na+]>O1CCCC1>[Cl:7][C:8]1[CH:24]=[CH:23][C:11]2[C:12]3[C:13]([CH3:21])([CH3:22])[CH2:14][CH2:15][NH:16][C:17]=3[CH2:18][CH2:19][C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 543287808-Chloro-1,1-dimethyl-1,2,5,6-tetrahydrobenzo[f]quinolin-3-one

Product 1

HCID 198331288-Chloro-1,1-dimethyl-1,2,3,4,5,6-hexahydrobenzo[f]quinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.36 g (0.089 mol) of lithium aluminium hydride are suspended in 100 ml of tetrahydrofuran under argon, 11.6 g (0.044 mol) of 8-chloro-1,1-dimethyl-1,2,5,6-tetrahydrobenzo[f]quinolin-3-one are slowly added thereto and the mixture is boiled under reflux for 2.5 hours. The mixture is then cooled to 0°, 12 ml of 18 percent sodium hydroxide solution are added dropwise thereto and the mixture is filtered. On evaporation of the filtrate, there is obtained 8-chloro-1,1-dimethyl-1,2,3,4,5,6-hexahydrobenzo[f]quinoline as a yellow oil which is processed directly.

Workup

  1. temperatureunder reflux for 2.5 hours
  2. temperatureThe mixture is then cooled to 0°
  3. filtrationthe mixture is filtered
  4. customOn evaporation of the filtrate

Sources & evidence

ORD record
ord-7261105add61431b8a1782a9ecb490db
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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